Dichloromethane → HCID 69810781, compound

HRID 1809450Notes

Reaction equation

HRID 1809450 reaction equation
C([O-])(O)=O.[Na+].[NH2:6][C:7]1[N:12]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[CH:10]=[CH:9][CH:8]=1.[C:17]([C:19]1[CH:28]=[CH:27][C:22]([C:23](=O)[CH2:24]Br)=[CH:21][CH:20]=1)#[N:18].C(Cl)Cl>CC(O)C>[C:17]([C:19]1[CH:28]=[CH:27][C:22]([C:23]2[N:6]=[C:7]3[CH:8]=[CH:9][CH:10]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[N:12]3[CH:24]=2)=[CH:21][CH:20]=1)#[N:18]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 986544-(Bromoacetyl)benzonitrileHCID 516892Sodium Bicarbonate2×HCID 13809143Methyl 6-aminopyridine-2-carboxylate

Product 1

HCID 69810781HCID 69810781, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

NaHCO3 (1.0 eq.) was added to a solution of (A1) in i-PrOH (0.5 M), then 4-cyanophenacyl bromide (1.2 eq.) was added and the resulting reaction mixture was stirred at RT for 18 h, then heated to reflux for another 18 h. After cooling down, the solvent was reduced in vacuo and the residue partioned between sat. aq. NaHCO3 and DCM. The aqueous phase was separated and extracted several times with DCM. The combined organic extracts were washed with brine and dried (Na2SO4). Evaporation of the solvent gave a residue which was triturated with hot EtOH and filtered to yield (31%) the title compound as a yellow solid. 1H NMR (400 MHz, DMSO-d6, 300K) δ 9.31 (1H, s), 8.26 (2H, d, J=8.3 Hz), 8.00 (1H, d, J=9.0 Hz), 7.91 (2H, d, J=8.3 Hz), 7.85 (1H, d, J=7.0 Hz), 7.45 (1H, dd, J=9.0, 7.0 Hz), 4.00 (3H, s). MS (ES+) C16H11N3O2 requires: 277, found: 278 (M+H)+.

Workup

  1. customthe resulting reaction mixture
  2. temperatureheated
  3. temperatureto reflux for another 18 h
  4. temperatureAfter cooling down
  5. customThe aqueous phase was separated
  6. extractionextracted several times with DCM
  7. washThe combined organic extracts were washed with brine
  8. dry with materialdried (Na2SO4)
  9. customEvaporation of the solvent
  10. customgave a residue which
  11. customwas triturated with hot EtOH
  12. filtrationfiltered

Sources & evidence

ORD record
ord-39d9d30e86e940f1b329491079324f24
Source dataset
uspto-grants-2013_01
Patent number
US08362030B2

Reaction notes

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